248256-10-2

Upstream product

• 89-95-2 2-methyl-benzyl alcohol 
• 2181-42-2 trimethylsulphonium iodide 
• 352-13-6 4-flourophenylmagnesium bromide 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 62666-37-9 (2-hydroxyphenyl)(4-fluorophenyl)methanone 
• 1829-34-1 2-hydroxy-3-bromobenzaldehyde 
• 533-58-4 2-Iodophenol 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 1258932-69-2 1-(4-fluorophenyl)-2-(2-iodophenoxy)ethan-1-one 
• 1508310-10-8 2-(1-(4-fluorophenyl)vinyl)phenol 
• 271-89-6 1-benzofurane 
• 460-00-4 1-Bromo-4-fluorobenzene 

Relevant academic research and scientific papers

Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives

A nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.

Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent

Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles

The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.

Cobalt(III)-Catalyzed Intramolecular Cross-Dehydrogenative C?H/X?H Coupling: Efficient Synthesis of Indoles and Benzofurans

An efficient cobalt(III)-catalyzed intramolecular cross-dehydrogenative C?H/N?H coupling of ortho-alkenylanilines has been developed utilizing O2as a terminal oxidant. The developed reaction tolerates various reactive functional groups and allo

Direct arylation of benzo[b]furan and other benzo-fused heterocycles

The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be accessible more elaborately using classical synthetic strategies. This is the first systematic study of the direct arylation of benzo[b]-furan.

Reactions of 2-hydroxybenzophenones with Corey-Chaykovsky reagent

A variety of 2-hydroxybenzophenones on reaction with Corey-Chaykovsky reagent underwent unprecedented rearrangements leading to 3-substituted benzofurans 8 and one-carbon homologated compounds 9 and 12. Compounds 9 could further be quantitatively transfor

A novel series of non-carboxylic acid, non-hydantoin inhibitors of aldose reductase with potent oral activity in diabetic rat models: 6-(5-Chloro-3- methylbenzofuran-2-sulfonyl)-2H-pyridazin-3-one and congeners

Discovery of a highly selective, potent, and safe non-carboxylic acid, non-hydantoin inhibitor of aldose reductase (AR) capable of potently blocking the excess glucose flux through the polyol pathway that prevails under diabetic conditions has been a long-standing challenge. In response, we did high-throughput screening of our internal libraries of compounds and identified 6-phenylsulfonylpyridazin-2H-3-one, 8, which showed modest inhibition of AR, both in vitro and in vivo. Initial structure-activity relationships concentrated on phenyl substituents and led to 6-(2,4-dichlorophenylsulfonyl)-2/f-pyridazin- 3-one, 81, which was more potent than 8, both in vitro and in vivo. Incorporation of extant literature findings with other aldose reductase inhibitors, including zopolrestat, resulted in the title inhibitor, 19m, which is one of the most potent and highly selective non-carboxylic acid, non-hydantoin inhibitors of AR yet described (IC50, 1 nM; ED 90 vs sciatic nerve sorbitol and fructose, respectively, 0.8 and 4.0 mg/kg). In rats, its oral bioavailability is 98% and it has a favorable plasma t1/2 (26 ± 3 h).

Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents

An efficient combinatorial route to substituted 3-phenyl-benzofurans, is achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification step.